Solvent Saturation-Transfer Effects in Pulsed-Field-Gradient Heteronuclear Single-Quantum-Coherence (PFG-HSQC) Spectra of Polypeptides and Proteins

Li, Yu-Chin; Montelione, Gaetano T.

doi:10.1006/jmrb.1993.1049

Cited by 43 publications

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“…The structural confirmation of saccharides 1 and 2 according to 1 H, 13 C NMR analyses and the subsequent complete assignment of 1 H, 13 C NMR signals were carried out using 2D NMR techniques, including COSY, 24,25) HSQC, 26) HSQC TOCSY 27) and HMBC. 28,29) Glucose and fructose residues of these saccharides are represented as Glc, Glc , Glc and Fru, as shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

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Isolation and Identification of Novel Tri- and Tetra-saccharides Synthesized by Thermoanaerobacter brockii Kojibiose Phosphorylase

Takahashi¹,

Fukushi²,

Onodera³

et al. 2007

J. Appl. Glycosci.

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Oligosaccharides are widely known to have benefical health effects. They are classified into homooligosaccharides such as xylooligosaccharide, maltooligosaccharide and inulooligosaccharide, and heterooligosaccharides such as fructooligosaccharide, galactooligosaccharide, soybeenoligosaccharide, raffinose and palatinose. Thus, they are thought to selectively increase bifidobacteria, 1) enhance immune responses, 2) promote the absorption of minerals, 3) and more recently, prevent diseases such as a heart diseases, hypertension, diabetes and osteoporosis.Palatinose is produced by treatment of sucrose with Protaminobacter rubrum, 4) and is used in various foods as sweeteners not causing dental caries. 5) Although palatinose is hydrolyzed more slowly than sucrose, this saccharide is finally absorbed in the small intestine. Changing this saccharide into a non digestible oligosaccharide is useful to improve the function.In recent years, the synthesis of oligosaccharides having various functions has been actively performed. These oligosaccharides are mostly synthesized using hydrolases and glycosyltransferases. The phosphorylases belonging to glycosyltransferases are also expected to give good results due to their reversible reaction, although there have been few studies.We have previously studied the production of indigestible oligosaccharides such as inulooligosaccharide, 6,7) fructooligosaccharide, 8) fructosylxyloside 9) and fructosyllactosucrose 10) using Penicillium purpurogenum inulinase,Scopulariopsis brevicaulis fructosyltransferase 8,9) and asparagus 1 F fructosyltransferase. 10 12) These oligosaccharides were shown to suppress the rise of serum glucose and insulin responses in rats, 13) and serum cholesterol 14) and triacylglycerol 15) in humans, and to have prebiotic effects. 15,16) Recently, our studies have involved the synthesis of novel oligosaccharides elongated with one, two or three additional glucose units by glucosyltransfer from β D glucose 1 phosphate to isokestose, nystose, 17) raffinose and stachyose 18) using Thermoanaerobacter brockii kojibiose phosphorylase. Now, we report the structural analysis and functional analysis of two novel oligosaccharides synthesized by glucosyltransfer from β D glucose 1 phosphate to palatinose using kojibiose phosphorylase. MATERIALS AND METHODS Saccharides.Crystalline palatinose (O α D glucopyranosyl (1 6) D fructofuranose) were purchased from Wako Pure Chemical Industries, Ltd., Osaka, Japan. Kojibiose and β D glucose 1 phosphate (β D G1P) were purchased from Sigma Chemical Co. (St. Louis, MO, USA).Enzyme. Kojibiose phosphorylase was purified from a cell free extract of T. brockii ATCC 35047. 19)High performance anion-exchange chromatography (HPAEC). The oligosaccharides was analyzed using a Dionex Bio LC Series apparatus equipped with a carbohydrate column (Carbo Pack PA 1, inert styrene divinylbenzene polymer) and a pulsed amperometric detector (PAD). 20,21) The mobile phase consisted of eluent A (150 mM NaOH) with a sodium acetate gradient as follows: 0 J. A...

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Section: Resultsmentioning

confidence: 99%

“…1 H 1 H COSY, 24,25) and HSQC 26) were obtained using gradient selected pulse sequences. The phase sensitive HSQC TOCSY spectra were determined with the sequence including inversion of direct resonance (IDR).…”

Section: Gas Liquid Chromatography (Gc)mentioning

confidence: 99%

Isolation and Identification of Novel Tri- and Tetra-saccharides Synthesized by Thermoanaerobacter brockii Kojibiose Phosphorylase

Takahashi¹,

Fukushi²,

Onodera³

et al. 2007

J. Appl. Glycosci.

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“…Isolation of saccharides was done by normal phase HPLC using amide-80 column. [13], and HMBC [14,15] spectra were obtained using gradient selected pulse sequences. The phase sensitive HSQC-TOCSY spectra were determined with the sequence including inversion of direct resonance (IDR) [16].…”

Section: Nmr Measurementsmentioning

confidence: 99%

Structural Analysis of Two Trisaccharides Isolated from Fermented Beverage of Plant Extract

Kawazoe¹,

Okada²,

Fukushi³

et al. 2008

TOGLYJ

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Fermented beverage of plant extract was prepared from about fifty kinds of vegetables and fruits. Natural fermentation was carried out mainly by lactic acid bacteria (Leuconostoc spp.) and yeast (Zygosaccharomyces spp.and Pichia spp.). Two novel oligosaccharides have been found from this beverage and isolated from the beverage using carbon-Celite column chromatography and preparative high performance liquid chromatography. Structure confirmation of the saccharides was provided by methylation analysis, MALDI-TOF-MS and NMR measurements. These saccharides were identified as new trisaccharides, -D-glucopyranosyl- (1 1

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“…The COSY 16,17) spectrum assigned the spin systems of these residues: from H 1 to H 6 in β Glc, from H 1 to H 5 of α Glc, and from H 4 to H 6 in Fru. The corresponding 13 C signals were assigned by HSQC 18) spectrum. The assignment of resting signals, the position of glycosidic linkage, and pyranoside form of fructose were analyzed as follows.…”

Section: Structure Analysis Of Saccharidesmentioning

confidence: 99%

Structural Analysis and Synthesis of Oligosaccharides Isolated from Fermented Beverage of Plant Extract

Okada¹,

Kawazoe²,

Yamamori³

et al. 2008

J. Appl. Glycosci.

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The extract from 50 kinds of fruits and vegetables was fermented to produce a new beverage.1,2) The juices were extracted using sucrose osmotic pressure in a cedar barrel for one week and were fermented by lactic acid bacteria (Leuconostoc spp.) and yeast (Zygosaccharomyces spp. and Pichia spp.). The fermented beverage showed scavenging activity against 1,1 diphenyl 2 picrylhydrazyl (DPPH) radical, and reduced significantly the ethanol induced damage to gastric mucosa in rats.1) Analysis by high performance anion exchange chromatography (HPAEC) showed that this beverage contained high levels of saccharides, estimated between 550 and 590 gL 1 , mainly glucose and fructose, and a small amount of undetermined oligosaccharides. Recently, it was reported that different positions of glycosidic linkage of oligosaccharide isomers affected physiological properties as well as physical properties.3 5) Development of HPLC analyses with high sensitivity and separation ability enables the detection and isolation of oligosaccharides in the fermented beverage.In this paper, we reported isolation and structure confirmation of the saccharides from fermented beverage of plant extract, and screening of yeast synthesizing novel saccharides was done. Preparation of fermented beverage of plant extract.For preparation of initial juice, fifty kinds of fruits and vegetables were used to produce the final extract as shown in a previous paper.1) Fruits and vegetables, obtained from the local markets of the Hokkaido region, were sorted for absence of defects or attacks, washed and immediately processed for juice extraction. The fifty fruits and vegetables were cut, sliced or diced in small pieces, mixed and put in cedar barrels. Afterwards, an equivalent weight of sucrose was added to samples, mixed well to allow high contact between samples and sucrose, and then barrels were left during one week at room temperature. Sucrose was almost completely hydrolyzed to glucose and fructose during fermentation. The juice exudates was then separated without compression from solids and used for fermentation. The fermented beverage was obtained by incubation of the juice at 37 C in the dark by natural fermentation using yeast (Zygosaccharomyces spp. and Pichia spp.) and lactic acid bacteria (Leuconostoc spp.). After 7 days, the fermented beverage was kept in a closed enameled tank at 37 C during six to ten months for additional maturation and aging, obtaining finally a brown and slightly sticky liquid.The pH of plant extract was about 3.2, reached after 7 days of fermentation (Fig. 1). Isolation of saccharides from fermented beverage of plant extract.Synthesis of saccharides by the fermentation of plant extract was investigated using the HPLC with p aminobenzoic acid ethyl ester (ABEE) conversion method.6,7) As shown in Fig. 2, various kinds of saccha-

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Solvent Saturation-Transfer Effects in Pulsed-Field-Gradient Heteronuclear Single-Quantum-Coherence (PFG-HSQC) Spectra of Polypeptides and Proteins

Cited by 43 publications

References 0 publications

Isolation and Identification of Novel Tri- and Tetra-saccharides Synthesized by Thermoanaerobacter brockii Kojibiose Phosphorylase

Isolation and Identification of Novel Tri- and Tetra-saccharides Synthesized by Thermoanaerobacter brockii Kojibiose Phosphorylase

Structural Analysis of Two Trisaccharides Isolated from Fermented Beverage of Plant Extract

Structural Analysis and Synthesis of Oligosaccharides Isolated from Fermented Beverage of Plant Extract

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